JP7032112B2 - 感光性樹脂組成物、複合体、積層構造物、並びにこれを用いたディスプレイ素子及び電子素子 - Google Patents
感光性樹脂組成物、複合体、積層構造物、並びにこれを用いたディスプレイ素子及び電子素子 Download PDFInfo
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- JP7032112B2 JP7032112B2 JP2017224304A JP2017224304A JP7032112B2 JP 7032112 B2 JP7032112 B2 JP 7032112B2 JP 2017224304 A JP2017224304 A JP 2017224304A JP 2017224304 A JP2017224304 A JP 2017224304A JP 7032112 B2 JP7032112 B2 JP 7032112B2
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- photosensitive resin
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- 239000002131 composite material Substances 0.000 description 7
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- 238000002161 passivation Methods 0.000 description 5
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- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 4
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
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-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/1336—Illuminating devices
- G02F1/133617—Illumination with ultraviolet light; Luminescent elements or materials associated to the cell
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Description
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
L’及びL”は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基である。
La乃至Ldは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
Ra及びRbは、それぞれ独立して水素原子又は下記化学式Cで表され、
Le乃至Lgは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R0は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基である。
L1乃至L10は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1及びR2は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlである。
前記化学式1において、Mは、Znであり得る。
前記R1及びR2は、それぞれ独立して下記化学式2A又は化学式2Bで表され得る。
L11は、置換若しくは非置換されたC1乃至C10アルキレン基であり、
R3は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
m1は、0又は1の整数である。
前記R1及びR2は、それぞれ独立して下記化学式2-1~化学式2-3からなる群より選ばれる何れか一つで表され得る。
L12乃至L15は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキレン基であり、
R4乃至R9は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基であり、
m2乃至m4は、それぞれ独立して0又は1の整数である。
L1乃至L10及びL16乃至L25は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1、R2、R10、及びR11は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
Xは、F、Cl、Br、又はIであり、
nは、1以上(例えば、2以上、3以上100以下、50以下、30以下、20以下、又は10以下)の整数である。
前記化学式3において、Mは、Znであり得る。
前記R1、R2、R10、及びR11は、それぞれ独立して下記化学式2A又は化学式2Bで表され得る。
L11は、置換若しくは非置換されたC1乃至C10アルキレン基であり、
R3は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
m1は、0又は1の整数である。
前記R1、R2、R10、及びR11は、それぞれ独立して下記化学式2-1~化学式2-3からなる群より選ばれる何れか一つで表され得る。
L12乃至L15は、それぞれ独立して置換若しくは非置換されたC1乃至C10アルキレン基であり、
R4乃至R9は、それぞれ独立して置換若しくは非置換されたC1乃至C10アルキル基であり、
m2乃至m4は、それぞれ独立して0又は1の整数である。
前記金属含有化合物は、前記光変換物質(例えば、表面)を囲む形態で存在し得る。
前記光変換物質は、その表面に硫黄原子を含み、前記金属含有化合物内の金属が前記光変換物質の表面の硫黄原子に結合され得る。
前記感光性樹脂組成物は、カルボキシ基含有バインダーポリマー(例えば、カルボキシ基含有アクリル系ポリマー)を更に含み得る。
前記感光性樹脂組成物は、拡散剤を更に含み得る。
前記拡散剤は、硫酸バリウム、炭酸カルシウム、二酸化チタン、ジルコニア、又はこれらの組み合わせを含み得る。
前記拡散剤は、前記感光性樹脂組成物の総重量に対して0.1重量%~20重量%で含まれ得る。
前記感光性樹脂組成物は、末端にチオール基を含む化合物を更に含み得る。
前記光変換物質は、量子ドットを含み得る。
前記感光性樹脂組成物は、前記感光性樹脂組成物の総重量に対して、前記(A)光変換物質が1重量%~50重量%と、前記(B-1)金属含有化合物が1重量%~50重量%(例えば、1重量%~30重量%)と、前記(C)光重合性単量体が0.1重量%~30重量%と、前記(D)光重合開始剤が0.1重量%~10重量%と、前記(E)溶媒の残部量と、を含み得る。
前記感光性樹脂組成物は、マロン酸;3-アミノ-1,2-プロパンジオール;シラン系カップリング剤;レベリング剤;フッ素系界面活性剤;又はこれらの組み合わせを更に含み得る。
前記感光性樹脂組成物は、25℃で120時間放置時、初期粘度に対する粘度増加率が10%以下であり得る。
前記繰り返し区画は、第1光と異なる波長の第2光を放出する第2区画を含み得る。
前記光変換層は、第3光を放出又は透過させる第3区画を更に含み得る。
前記光源は、有機発光素子であり得る。
前記電子素子は、LED、OLED、センサ、太陽電池、又はディスプレイ装置であり得る。
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
L’及びL”は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基である。
La乃至Ldは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
Ra及びRbは、それぞれ独立して水素原子又は下記化学式Cで表され、
Le乃至Lgは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R0は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基である。
L1乃至L10は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1及びR2は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlである。
L11は、置換若しくは非置換されたC1乃至C10アルキレン基であり、
R3は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
m1は、0又は1の整数である。
L12乃至L15は、それぞれ独立して置換若しくは非置換されたC1乃至C10アルキレン基であり、
R4乃至R9は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基であり、
m2乃至m4は、それぞれ独立して0又は1の整数である。
L1乃至L10及びL16乃至L25は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1、R2、R10、及びR11は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
Xは、F、Cl、Br、又はIであり、
nは、1~100の整数である。
L26及びL27は、それぞれ独立して単一結合、置換若しくは非置換されたC1乃至C20アルキレン基、置換若しくは非置換されたC3乃至C20シクロアルキレン基、置換若しくは非置換されたC6乃至C20アリーレン基、又は置換若しくは非置換されたC2乃至C20ヘテロアリーレン基である。
L26及びL27は、それぞれ独立して単一結合、置換若しくは非置換されたC1乃至C20アルキレン基、置換若しくは非置換されたC3乃至C20シクロアルキレン基、置換若しくは非置換されたC6乃至C20アリーレン基、又は置換若しくは非置換されたC2乃至C20ヘテロアリーレン基であり、
u1及びu2は、それぞれ独立して0又は1の整数である。
Ra、Rb、Rc、及びRdは、それぞれ独立して下記化学式6-1~化学式6-3のうちの何れか一つで表される。
m2乃至m4は、それぞれ独立して0又は1の整数である。
Reは、上記化学式6-2で表される。
(分散剤の投入含有量は、緑色量子ドット固形分対比15重量%である。)
InP/ZnS量子ドット(fluorescence λem=525nm、FWHM=40nm、GreenQD、ハンソルケミカル社製)
(B-1-a)合成例1で製造された金属含有化合物
(B-1-b)合成例2で製造された金属含有化合物
(B-2-a)アクリル系バインダー樹脂(SM-400H、SMS社製)酸価:130mgKOH/g
(B-2-b)アクリル系バインダー樹脂(NPR1520、ミウォン商社)酸価:125 mgKOH/g
ペンタエリスリトールヘキサメタクリレート(DPHA、日本化薬社製)
ジフェニル(2,4,6-トリメチルベンゾイル)ホスフィンオキシド(TPO、Sigma-Aldrich社製)
(E-1)シクロヘキサン(Sigma-Aldrich社製)
(E-2)プロピレングリコールモノメチルエーテルアセテート(PGMEA、Sigma-Aldrich社製)
二酸化チタン分散液(TiO2固形分20重量%、平均粒径:200nm、dittotechnology(株)製)
グリコールジ-3-メルカプトプロピオナート(BRUNO BOCK社製)
フッ素系界面活性剤(F-554、DIC社製)
金属含有化合物の代わりにZnCl2を更に使用したことを除いては、実施例3と同様にして、比較例3による感光性樹脂組成物を製造した。
120 導光板
200 液晶パネル
210 下部基板
211 配線板
220 液晶層
221 配向膜
230 自発光カラーフィルタ層
231 透明共通電極
240 上部基板
241 ブラックマトリックス
300 光学素子(偏光板)
Claims (33)
- 感光性樹脂組成物であって、
(A)光変換物質と、
(B-1)金属含有化合物と、
(C)光重合性単量体と、
(D)光重合開始剤と、
(E)溶媒と、を有し、
前記金属含有化合物は、*-S-M-S-*(Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTl)で表される残基を含み、下記化学式Aで表される構造を含むことを特徴とする感光性樹脂組成物。
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
L’及びL”は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基である。 - 前記金属含有化合物は、下記化学式Bで表される構造単位を含むことを特徴とする請求項1に記載の感光性樹脂組成物。
La乃至Ldは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
Ra及びRbは、それぞれ独立して水素原子、置換若しくは非置換されたC1乃至C10アルキル基、又は下記化学式Cで表され、
Le乃至Lgは、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R0は、置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基である。 - 前記金属含有化合物は、下記化学式1で表される構造単位を含むことを特徴とする請求項1に記載の感光性樹脂組成物。
L1乃至L10は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1及びR2は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlである。 - 前記Mは、Znであることを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記金属含有化合物は、下記化学式3で表されることを特徴とする請求項1に記載の感光性樹脂組成物。
L1乃至L10及びL16乃至L25は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基であり、
R1、R2、R10、及びR11は、それぞれ独立して置換若しくは非置換されたC1乃至C20アルキル基、置換若しくは非置換されたC3乃至C20シクロアルキル基、又は置換若しくは非置換されたC7乃至C20ビシクロアルキル基であり、
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
Xは、F、Cl、Br、又はIであり、
nは、1~100の整数である。 - 前記Mは、Znであることを特徴とする請求項7に記載の感光性樹脂組成物。
- 前記金属含有化合物は、1,000g/mol~15,000g/molの重量平均分子量を有することを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記金属含有化合物と前記光変換物質とは、前記金属含有化合物が前記光変換物質の表面を囲む形態で存在することを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記光変換物質は、その表面に硫黄原子を含み、前記金属含有化合物が前記光変換物質の表面に結合されることを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、カルボキシ基含有バインダー樹脂を更に含むことを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、拡散剤を更に含むことを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記拡散剤は、硫酸バリウム、炭酸カルシウム、二酸化チタン、ジルコニア、又はこれらの組み合わせを含むことを特徴とする請求項15に記載の感光性樹脂組成物。
- 前記拡散剤は、前記感光性樹脂組成物の総量に対して0.1重量%~20重量%で含まれることを特徴とする請求項15に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、末端にチオール基を含む有機チオール化合物を更に含むことを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記光変換物質は、量子ドットを含むことを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、前記感光性樹脂組成物の総量に対して、
前記(A)光変換物質が1重量%~50重量%と、
前記(B-1)金属含有化合物が1重量%~50重量%と、
前記(C)光重合性単量体が0.1重量%~50重量%と、
前記(D)光重合開始剤が0.1重量%~10重量%と、
前記(E)溶媒の残部量と、を含むことを特徴とする請求項1に記載の感光性樹脂組成物。 - 前記感光性樹脂組成物は、マロン酸;3-アミノ-1,2-プロパンジオール;シラン系カップリング剤;レベリング剤;フッ素系界面活性剤;又はこれらの組み合わせを更に含むことを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、25℃で初期粘度が1cPs以上100cPs以下であることを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物は、25℃で120時間放置時、初期粘度に対する粘度増加率が10%以下であることを特徴とする請求項1に記載の感光性樹脂組成物。
- ポリマーマトリックス及び前記ポリマーマトリックス内に分散された光変換物質を含み、
前記ポリマーマトリックスは、*-S-M-S-*(Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTl)で表される残基及びエステル連結基を含み、下記化学式Aで表される構造を含むことを特徴とする複合体。
Mは、Zn、Al、Mg、Ca、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Ga、Sr、Y、Zr、Nb、Mo、Cd、In、Ba、Au、Hg、又はTlであり、
L’及びL”は、それぞれ独立して単一結合又は置換若しくは非置換されたC1乃至C10アルキレン基である。 - 前記光変換物質は、前記*-S-M-S-*で表される残基によってパッシベーションされていることを特徴とする請求項24に記載の複合体。
- 基板及び前記基板上に配置された光変換層を含み、
前記光変換層は、予め定められた波長の光を放出する一つ以上の繰り返し区画を含み、
前記繰り返し区画は、請求項24に記載の複合体を含むことを特徴とする積層構造物。 - 請求項26に記載の積層構造物、及び前記積層構造物に入射光を提供する光源を含むことを特徴とするディスプレイ素子。
- 前記ディスプレイ素子は、前記光源を含むバックライトユニット、及び前記バックライトユニット上に位置する液晶パネルを含み、
前記液晶パネルは、下部基板、前記下部基板の反対側に配置された上部基板、及び前記上部基板と下部基板との間に介在する液晶層を含み、
前記光変換層は、前記液晶層に対面するように配置されることを特徴とする請求項27に記載のディスプレイ素子。 - 前記ディスプレイ素子は、前記液晶パネルの下に偏光子を更に含むことを特徴とする請求項28に記載のディスプレイ素子。
- 前記ディスプレイ素子は、前記液晶層と前記光変換層との間に偏光子を更に含むことを特徴とする請求項28に記載のディスプレイ素子。
- 前記光源は、有機発光素子であることを特徴とする請求項28に記載のディスプレイ素子。
- 請求項26に記載の積層構造物を含むことを特徴とする電子素子。
- 前記電子素子は、ディスプレイ素子、有機発光装置(organic light emitting diode)、及びセンサを含むことを特徴とする請求項32に記載の電子素子。
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